Sean Pavone / Shutterstock5 of the Coolest Places You Can Fly to for Around $500 Hannah Winsten August 26, 2015 Adventure Travel, Arts & Culture, Beach Vacations, Caribbean, Family Travel, Food & Drink, Interests, International Travel, Photography, Shopping, Trending Stories, Weddings and Romance 11 Comments This post was most recently updated on March 14th, 2016Labor Day may have (almost) passed, my lovelies, but don’t despair. You can totally still travel far and wide, and you’ve got the perfect excuse to take a nice, long, extended trip. We’re giving away a $500 CheapOair gift card to one lucky winner on Tuesday, September 8—and that means you might be traveling somewhere post-Labor Day, on us! Now that’s what I call travel inspiration. I’m sure you’ve already clicked away from this post to enter into that giveaway—and if you haven’t, what are you doing? That’s a $500 gift card, people! Go enter that giveaway right now! But just in case you’re still with us, we’ve got a few AWESOME suggestions for what to do with that fabulous prize. So, where can you go for around $500? Here are 5 of the coolest places you can hit if you win our giftcard!* *The advertised destinations below are based on air ticket bookings made on CheapOair.com after September 8, 2014 for travel between September 22nd and November 30th, 2014. Fares are roundtrip and include taxes and fees. Fares are based on historical data, are subject to change, and cannot be guaranteed at the time of booking. 1.) Kingston, Jamaica Mehdi Kasumov / Shutterstock If you’re looking for an amazing beach vacation—with a side of adventure—Jamaica’s the place for you. This Caribbean island nation can be the epitome of luxury and relaxation, or an adrenaline junkie’s dream. The choice is yours! If relaxation is what you’re after, grab an adult beverage and sink your toes into the sand. Spend a week lying in the sun, swimming in the crystal blue waters, and eating ridiculously delicious Jamaican food. Calories don’t count on vacation, remember? If you’d rather do a little more than lie around with your toes in the sand, you can zip line through the jungle, swim with dolphins, sharks, and stingrays, or jump off the famed Jamaican cliffs into crystal blue waters below. Even crazier, you can go bobsledding through the jungle! Jamaica’s got an Olympic-level bobsledding team, and you can experience the quirky sport’s thrill, sans ice and snow. That sounds like the ideal way to go bobsledding, am I right? 2.) Nassau, Bahamas nicolas.voisin44 / Shutterstock Get ready for a ton of beach options, folks. The island chain of the Bahamas has more than 700 unique islands and cays, meaning you’ve got the pick of the litter when it comes to choosing the perfect square of sand to plop yourself down onto for a few days. If you’re looking for luxury, head over to New Providence Island for gorgeous resorts, casinos, and golf courses. Keep an eye out for your old prep school buddies! If you’re more of a nature lover, swing by Grand Bahama, where you can tour underwater limestone caves and botanical gardens. No matter which island you hit on the Bahamas, most will allow you to go snorkeling, fishing, scuba diving, and more. You might even get to swim with dolphins! SOLD. The quirkiest thing you can do in the Bahamas? Take a tour of the cays, each of which is weirder and more idiosyncratic than the last. One cay is inhabited by a family of adorable, wild pigs who will doggy-paddle their way out to meet your approaching boat. Caribbean beach vacations don’t get much more Instagram-able than that. 3.) Myrtle Beach, SC Sean Pavone / Shutterstock One of the most family-friendly beach destinations you could possibly hope for, get ready for a fun-filled getaway that everyone will enjoy! There are miles of pristine beaches for the adults—and let’s be real, the kids will love the beach too—filled with the brown sand that the region’s famous for. When you need a break from vegging out on the beach, visit one of the area’s many golf courses, or bring the kids to one of the nearby amusement parks in town! Other highlights include Ripley’s Aquarium and a Dixie Stampede Dinner show. Yee-haw! 4.) New York City, NY dibrova / Shutterstock Not a beach bunny? Never fear. The period between late summer and early fall is the perfect time to visit the Big Apple, with moderate weather, smaller crowds, and lower accommodation prices. What to do once you get here? The beauty of the city lies in its neighborhoods, so hop on a double decker bus or take a walking tour to get a lay of the land. Make sure you check out Greenwich Village during the day for its gorgeous parks and local art scene, then hit up the Lower East Side after dark for exciting nightlife. Other must-sees? Central Park and the Empire State Building should be on your to-do list, as well as climbing to the Top of the Rock for an amazing view in the city. Awesome! 5.) New Orleans, LA Curioso / Shutterstock If New York’s a little too crazy for you, head down to New Orleans for the ultimate cultural extravaganza. Set up camp in the French Quarter, the historic part of town where you’ll find ridiculously good food and lots of old, fancy architecture. In the evenings, make sure to check out some live music—jazz, specifically—as this is NOLA’s true claim to fame. For a look into the local Creole culture, head out on a Voodoo shopping tour. And of course, don’t forget to eat plenty of beignets! Who knew you could go to so many cool places for around such an affordable price? Where would you go if you won our $500 giftcard? Feel free to let us know in the comments, and then head over to our Facebook page and enter the giveaway!